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Chemistry

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Also known as: 2-(dimethylamino)ethanol, N,n-dimethylethanolamine, 108-01-0, Dimethylaminoethanol, Dimethylethanolamine, 2-dimethylaminoethanol
Molecular Formula
C4H11NO
Molecular Weight
89.14  g/mol
InChI Key
UEEJHVSXFDXPFK-UHFFFAOYSA-N
FDA UNII
2N6K9DRA24

Dimethylethanolamine
Deanol is commonly referred to as 2-(dimethylamino)ethanol, dimethylaminoethanol (DMAE) or dimethylethanolamine (DMEA). It holds tertiary amine and primary alcohol groups as functional groups. Deanol has been used in the treatment of attention deficit-hyperactivity disorder (ADHD), Alzheimer's disease, autism, and tardive dyskinesia. It has been also used as an ingredient in skin care, and in cognitive function- and mood-enhancing products.
1 2D Structure

Dimethylethanolamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(dimethylamino)ethanol
2.1.2 InChI
InChI=1S/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3
2.1.3 InChI Key
UEEJHVSXFDXPFK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)CCO
2.2 Other Identifiers
2.2.1 UNII
2N6K9DRA24
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 2-(dimethylamino)ethanol

2. N,n-dimethylethanolamine

3. 108-01-0

4. Dimethylaminoethanol

5. Dimethylethanolamine

6. 2-dimethylaminoethanol

7. Norcholine

8. Dmae

9. Dmea

10. Bimanol

11. Liparon

12. N,n-dimethylaminoethanol

13. Varesal

14. Propamine A

15. (2-hydroxyethyl)dimethylamine

16. Ethanol, 2-(dimethylamino)-

17. Kalpur P

18. Dimethylmonoethanolamine

19. Dimethylaminoaethanol

20. N,n-dimethyl-2-aminoethanol

21. Amietol M 21

22. N,n-dimethyl-2-hydroxyethylamine

23. N-dimethylaminoethanol

24. 2-(n,n-dimethylamino)ethanol

25. Dimethyl(hydroxyethyl)amine

26. Texacat Dme

27. Dimethylaethanolamin

28. Dimethyl(2-hydroxyethyl)amine

29. 2-(dimethylamino)-1-ethanol

30. N,n-dimethyl Ethanolamine

31. N-(2-hydroxyethyl)dimethylamine

32. N,n-dimethyl-n-(2-hydroxyethyl)amine

33. 2-(dimethylamino) Ethanol

34. (dimethylamino)ethanol

35. Beta-hydroxyethyldimethylamine

36. 2-dimethylamino-ethanol

37. Beta-dimethylaminoethyl Alcohol

38. 2-(dimethylamino)ethan-1-ol

39. 2-dwumetyloaminoetanolu

40. N-(dimethylamino)ethanol

41. N,n-dimethyl-n-(beta-hydroxyethyl)amine

42. Tegoamin Dmea

43. Nsc 2652

44. Dabco Dmea

45. Deanol [ban]

46. 2-dimethylamino Ethanol

47. N,n-dimethyl(2-hydroxyethyl)amine

48. N,n'-dimethylethanolamine

49. 2-(dimethylamino)-ethanol

50. (ch3)2nch2ch2oh

51. Chembl1135

52. .beta.-(dimethylamino)ethanol

53. 2n6k9dra24

54. .beta.-hydroxyethyldimethylamine

55. .beta.-dimethylaminoethyl Alcohol

56. Chebi:271436

57. Phosphatidyl-n-dimethylethanolamine

58. Nsc-2652

59. Deanol (ban)

60. N,n-dimethylaminoethanol (dmae)

61. Ncgc00159413-02

62. N,n-dimethyl-n-(.beta.-hydroxyethyl)amine

63. Dsstox_cid_505

64. Dsstox_rid_75628

65. Dsstox_gsid_20505

66. Deanol (n,n-dimethylethanolamine)

67. Demanol

68. Demanyl

69. Tonibral

70. Cas-108-01-0

71. Dimethylaethanolamin [german]

72. Dimethylamino Ethanol

73. Dimethylaminoaethanol [german]

74. Ccris 4802

75. 2-dwumetyloaminoetanolu [polish]

76. Hsdb 1329

77. Einecs 203-542-8

78. Un2051

79. Brn 1209235

80. N,n-dimethyl-n-ethanolamine

81. Unii-2n6k9dra24

82. Ai3-09209

83. Dimethylethanoiamine

84. Toyocat -dma

85. Dimethyl Ethanolamine

86. Dimethyl-ethanolamine

87. Mfcd00002846

88. Paresan (salt/mix)

89. Dimethyl Ethanol Amine

90. 2-dimethyamino-ethanol

91. N,n-dimethylethanolamin

92. Biocoline (salt/mix)

93. N,n Dimethylaminoethanol

94. Deanol [who-dd]

95. Deanol [mi]

96. N,n-dimethyl-ethanolamine

97. N,n-dimethylamino Ethanol

98. N,n-dimethylethanol Amine

99. N,n-dimethylethanol-amine

100. Deanol [mart.]

101. 2-hydroxyethyldimethylamine

102. 2-dimethylaminoethanol [un2051] [corrosive]

103. Ec 203-542-8

104. Beta -(dimethylamino)ethanol

105. Dimethyl Mea [inci]

106. Dimethylaminoaethanol(german)

107. Choline Chloride (salt/mix)

108. Luridin Chloride (salt/mix)

109. Beta -hydroxyethyldimethylamine

110. N,n-dimethylethanolamine/dmea

111. Beta -dimethylaminoethyl Alcohol

112. 2-(n,n-dimethyl Amino)ethanol

113. 2-(n,n-dimethylamino) Ethanol

114. Dtxsid2020505

115. N-hydroxyethyl-n,n-dimethylamine

116. 2-(n,n-dimethyl Amino) Ethanol

117. Ni(1/4)oen-dimethylethanolamine

118. Nsc2652

119. Beta -(dimethylamino)ethyl Alcohol

120. 2-hydroxy-n,n-dimethylethanaminium

121. Wln: Q2n1 & 1

122. 2-dimethylaminoethanol, >=99.5%

123. Bcp22017

124. Cs-m3462

125. Zinc1641058

126. .beta.-(dimethylamino)ethyl Alcohol

127. N, N-dimethyl(2-hydroxyethyl)amine

128. Tox21_113163

129. Tox21_201821

130. Tox21_302844

131. Bdbm50060526

132. N,n-dimethyl-beta -hydroxyethylamine

133. Stl282730

134. Dimethylaminopropylamine Reagent Grade

135. N-(2-hydroxyethyl)-n,n-dimethylamine

136. Akos000118738

137. N,n-dimethyl-.beta.-hydroxyethylamine

138. Db13352

139. N,n-dimethylethanolamine [hsdb]

140. Un 2051

141. N, N-dimethyl-n-(2-hydroxyethyl)amine

142. Ncgc00159413-03

143. Ncgc00256454-01

144. Ncgc00259370-01

145. Bp-13447

146. N,n-dimethyl-n-(beta -hydroxyethyl)amine

147. Db-002821

148. N, N-dimethyl-n-(beta -hydroxyethyl)amine

149. D0649

150. D07777

151. 2-dimethylaminoethanol [un2051] [corrosive]

152. 2-dimethylaminoethanol, Purum, >=98.0% (gc)

153. Q241049

154. 2-dimethylaminoethanol, Analytical Reference Material

155. 2-dimethylaminoethanol, Saj First Grade, >=99.0%

156. W-108727

157. N,n-dimethylethanolamine 100 Microg/ml In Acetonitrile

158. 2-dimethylaminoethanol, Purified By Redistillation, >=99.5%

159. N,n-dimethyl-2-hydroxyethylamine, N,n-dimethylethanolamine, Dmea

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 89.14 g/mol
Molecular Formula C4H11NO
XLogP3-0.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass89.084063974 g/mol
Monoisotopic Mass89.084063974 g/mol
Topological Polar Surface Area23.5 Ų
Heavy Atom Count6
Formal Charge0
Complexity28.7
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Antidepressive Agents; Anti-Dyskinesia Agents; An antidepressive agent that has also been used in the treatment of movement disorders. The mechanism of action is not well understood.

National Library of Medicine's Medical Subject Headings online file (2015 MeSH); Available from, as of February 23, 2015: https://www.nlm.nih.gov/cgi/mesh/2015/MB_cgi?term=Deanol


DMAE has been tested for its efficacy in treating a variety of diseases possibly related to deficiencies of acetylcholine with mixed results. Three reported no benefit from DMAE treatment (tardive dyskinesia; cognitive dysfunction; Alzheimer's disease). Benefits from DMAE treatment were found in other studies evaluating DMAE's ability to increase theta power or concentration. Centrophenoxine showed benefits for patients with organic psychosyndrome.[NTP; Dimethylethanolamine (DMAE)

108-01-0] and Selected Salts and Esters (November 2002); Available from, as of February 23, 2015: https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/dmae_update_110002_508.pdf


No beneficial effects were obtained when deanol was administered to 11 patients with tardive dyskinesia of long duration. Doses of deanol were increased gradually over a period of 9 days until a level of 400 mg 4 times a day was reached; this dose level was then maintained for an additional 9 days. /Former use/

Crane GE; N. Engl. J. Med.; 292: 926 (1975)


Two case reports are presented in which deanol (I) was used unsuccessfully to treat tardive dyskinesia. The first case report involved an 89-yr-old male with a 50 yr history of chronic paranoid schizophrenia and symptoms of tardive dyskinesia. I was administered in doses ranging from 450 to 600 mg daily for 5 months but had to be discontinued due to the development of marked sialism, bronchospasm, and parkinson rigidity. No change in the patient's tardive dyskinesia was noted. A second patient with tardive dyskinesia and a 30 yr history of schizophrenia received up to 800 mg daily of I for 5 months with no improvement noted. /Former use/

Mathew P et al; Am. J. Psychiatry; 133: 1467 (1976)


For more Therapeutic Uses (Complete) data for 2-DIMETHYLAMINOETHANOL (10 total), please visit the HSDB record page.


4.2 Drug Warning

Principal contraindication to its use is grand mal epilepsy.

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-240


Serious cholinergic side effects were reported in a 37-yr-old woman with tardive dyskinesia who had been taking deanol. Deanol was given for 19 days in increasing doses. After 17 days, while receiving 1.5 g/day, the patient began to experience symptoms.

Nesse R Carroll BJ; Lancet; 2 (3): 50-51(1976)


Deanol (400-6000 mg/day for 1-4 mo) admin to pt with involuntary movement disorders produced mood changes (depression or hypomania) only in those pt with tardive dyskinesia with a past history of psychiatric disorders.

CASEY DE; PSYCHOPHARMACOLOGY (BERLIN) 62(2) 187 (1979)


A large number of adverse health effects were associated with DMAE, including cardiovascular, neurological, and/or psychological effects. Specific attribution of adverse effects to DMAE is unlikely, as many of these products also contained Ephedra vulgaris alkaloids and other Ephedra spp.[NTP; Dimethylethanolamine (DMAE)

108-01-0] and Selected Salts and Esters (November 2002); Available from, as of February 23, 2015: https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/dmae_update_110002_508.pdf


For more Drug Warnings (Complete) data for 2-DIMETHYLAMINOETHANOL (6 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06B - Psychostimulants, agents used for adhd and nootropics

N06BX - Other psychostimulants and nootropics

N06BX04 - Deanol


5.2 Absorption, Distribution and Excretion

Daily oral exposures (deanol acetamidobenzoate, DMAE, or Deaner) of chinchilla rabbits or humans produced measurable plasma and cerebrospinal concentrations of the parent compound. The drugs were cleared from the plasma by 36 hours post-treatment.[NTP; Dimethylethanolamine (DMAE)

108-01-0] and Selected Salts and Esters (November 2002); Available from, as of February 23, 2015: https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/dmae_update_110002_508.pdf


Specific methods utilizing combined gas chromatography mass spectrometry were used to measure the metabolism of [(2)H6]deanol and its effects on acetylcholine concentration in vitro and in vivo. In vitro [(2)H6]deanol was rapidly taken up by rat brain synaptosomes, but was neither methylated nor acetylated. [(2)H6]Deanol was a weak competitive inhibitor of the high affinity transport of [(2)H4]choline, thus reducing the synthesis of [(2)H4]acetylcholine. In vivo [(2)H6]deanol was present in the brain after i.p. or p.o. administration, but was not methylated or acetylated. Treatment of rats with [(2)H6]deanol significantly increased the concentration of choline in the plasma and brain but did not alter the concentration of acetylcholine in the brain. Treatment of rats with atropine (to stimulate acetylcholine turnover) or with hemicholinium-3 (to inhibit the high affinity transport of choline) did not reveal any effect of [(2)H6]deanol on acetylcholine synthesis in vivo. However, since [(2)H6]deanol did increase brain choline, it may prove therapeutically useful when the production of choline is reduced or when the utilization of choline for the synthesis of acetylcholine is impaired.

PMID:512912 Jope RS, Jenden DJ; J Pharmacol Exp Ther. 211 (3) :472-9 (1979)


DMAE is absorbed and rapidly transported to the liver where much of it is metabolized. Approximately 280 nmol (25.2 ug) DMAE/gram plasma was observed in male mice about ten minutes after receiving 300 mg (3.30 mmol) DMAE/kg, intraperitoneally. Approximately 2.41, 1.30, and 0.20% of an administered dose of 30 mg/kg (0.13 mmol/kg) (with 100 u Ci) of (14)Cyprodenate was found in the liver, brain, and plasma, respectively, five minutes after intravenous dosing in male rats.[NTP; Dimethylethanolamine (DMAE)

108-01-0] and Selected Salts and Esters (November 2002); Available from, as of February 23, 2015: https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/dmae_update_110002_508.pdf


5.3 Metabolism/Metabolites

In male Wistar rats, DMAE was oxidized rapidly to the N-oxide of DMAE, representing the primary urinary metabolite. However, only 13.5 % of the administered dose was eliminated by the 24 hour time point, suggesting that most of the DMAE was routed toward phospholipid biosynthetic pathways. In humans, 33% of an injected 1 g (10 mmol) dose of DMAE was excreted unchanged. It was suggested that the remaining dose might have been demethylated to ethanolamine directed toward normal metabolic pathways.[NTP; Dimethylethanolamine (DMAE)

108-01-0] and Selected Salts and Esters (November 2002); Available from, as of February 23, 2015: https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/dmae_update_110002_508.pdf


Dimethylaminoethanol /prc: postulated to/ undergo endogenous methylation. /From table/

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 171


Specific methods utilizing combined gas chromatography mass spectrometry were used to measure the metabolism of [(2)H6]deanol and its effects on acetylcholine concentration in vitro and in vivo. In vitro [(2)H6]deanol was rapidly taken up by rat brain synaptosomes, but was neither methylated nor acetylated. [(2)H6]Deanol was a weak competitive inhibitor of the high affinity transport of [(2)H4]choline, thus reducing the synthesis of [(2)H4]acetylcholine. In vivo [(2)H6]deanol was present in the brain after i.p. or p.o. administration, but was not methylated or acetylated. Treatment of rats with [(2)H6]deanol significantly increased the concentration of choline in the plasma and brain but did not alter the concentration of acetylcholine in the brain. Treatment of rats with atropine (to stimulate acetylcholine turnover) or with hemicholinium-3 (to inhibit the high affinity transport of choline) did not reveal any effect of [(2)H6]deanol on acetylcholine synthesis in vivo. However, since [(2)H6]deanol did increase brain choline, it may prove therapeutically useful when the production of choline is reduced or when the utilization of choline for the synthesis of acetylcholine is impaired.

PMID:512912 Jope RS, Jenden DJ; J Pharmacol Exp Ther. 211 (3) :472-9 (1979)


Choline (N,N,N-trimethylethanolamine), which is widely distributed in membrane lipids and is a component of sediment biota, has been shown to be utilized anaerobically by mixed prokaryote cultures to produce methane but not by pure cultures of methanogens. Here, we show that five recently isolated Methanococcoides strains from a range of sediments (Aarhus Bay, Denmark; Severn Estuary mudflats at Portishead, United Kingdom; Darwin Mud Volcano, Gulf of Cadiz; Napoli mud volcano, eastern Mediterranean) can directly utilize choline for methanogenesis producing ethanolamine, which is not further metabolized. Di- and monomethylethanolamine are metabolic intermediates that temporarily accumulate. Consistent with this, dimethylethanolamine was shown to be another new growth substrate, but monomethylethanolamine was not. The specific methanogen inhibitor 2-bromoethanesulfonate (BES) inhibited methane production from choline. When choline and trimethylamine are provided together, diauxic growth occurs, with trimethylamine being utilized first, and then after a lag (about 7 days) choline is metabolized. Three type strains of Methanococcoides (M. methylutens, M. burtonii, and M. alaskense), in contrast, did not utilize choline. However, two of them (M. methylutens and M. burtonii) did metabolize dimethylethanolamine. These results extend the known substrates that can be directly utilized by some methanogens, giving them the advantage that they would not be reliant on bacterial syntrophs for their substrate supply.

PMID:23001649 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3497383 Watkins AJ et al; Appl Environ Microbiol. 78 (23): 8298-303 (2012)


For more Metabolism/Metabolites (Complete) data for 2-DIMETHYLAMINOETHANOL (8 total), please visit the HSDB record page.


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28-Jan-2021
10-Jun-2024
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Quantity (KGS) & Unit rate (USD/KGS) over time

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FDF Dossiers

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01

DDL Conference
Not Confirmed
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DDL Conference
Not Confirmed

Dimethylaminoethanol

Brand Name : Gericomplex

Dosage Form : CAP

Dosage Strength : 20mg

Packaging : 30X1mg

Approval Date :

Application Number :

Regulatory Info : Originator

Registration Country : South Africa

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02

DDL Conference
Not Confirmed
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DDL Conference
Not Confirmed

Dimethylaminoethanol

Brand Name : Gericomplex

Dosage Form : CAP

Dosage Strength : 20mg

Packaging : 100X1mg

Approval Date :

Application Number :

Regulatory Info : Originator

Registration Country : South Africa

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